Tetrabutylammonium Fluoride → ((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methanol

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Reaction Steps

To a solution of tert-butyldiphenyl(((5S,6aR)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)silane (from step 7) (7.2 g, 0.0169 mol) in 50 mL of anhydrous THF at 0° C., TBAF (20.28 mL, 0.0203 mol) was added and stirred at room temperature for 3 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated to dryness. Purified by column chromatography using hexane and ethyl ether as a gradient mixture to give 2.72 g of the title compound in 82% yield.

Provenance & Evidence